Vacation rentals in Wailea, Wailea-Makena

4.81 out of 5 average rating, 100 reviews

Top Floor/Artistic Island Vibes/Premier Location!

Featured property by a Super Host! LOCATION LOCATION LOCATION! Literally less than 3 minutes walking distance to the best beach in Maui! Unique because every piece of wall space in this unit is truly an artistic masterpiece. Huge step above any competition with a central A/C split system (Super Rare) & a zone for every room. Steps to the best beach which is also home to many restaurants, bars & shopping. Surf Boards and Toys! **Host was featured on HGTV House Hunters International.

Apartment in Wailea-Makena

5 out of 5 average rating, 10 reviews

A.R.A Retreats: Ocean Breeze

Located in Wailea Ekolu, the well-known luxury resort community of Wailea, this condo features beautiful ocean views from the living areas and primary bedroom. Relax and unwind after you spend all day taking in the sunshine around the island on the spacious ocean-facing lanai with comfortable seating. The moment you arrive, stepping into your private retreat, you’ll feel the unique charm of this special place—a favorite getaway for both first-time visitors and returning guests year after year.

Top guest favourite

Home in Kihei

5 out of 5 average rating, 10 reviews

Beautiful Beachfront Townhouse !

OUR MAUI BEACH HOUSE... This is the perfect place for a family vacation and retreat!! And it is right on the beach! Many of our guests enjoy staying right on our property or on our beach -- no need to leave. A very large two bedroom, three bath custom redwood townhouse we built in 1977 as a family retreat, with a fully-equipped kitchen and laundry. This is a comfortable beach house and we have done remodeling, refurnishing and updating recently. The master bedroom has huge ocean views.

4.89 out of 5 average rating, 157 reviews

*** Beautiful Oceanfront Maui Condo ***

🌴☀️🌴 TOURISM WELCOME! We are a fully legal Short Term Vacation Rental (STVR) condo and have been Superhosts on Airbnb for 10+ years. While Lahaina town is closed, the rest of the island (including areas of West Maui) is open, and visitors are welcome. Respectful tourism is highly encouraged. Please feel free to book any open dates on our calendar and Mahalo for helping to support Maui. 🌴☀️🌴 Come explore Maui from our beautiful centrally located Oceanfront Condo right on Sugar Beach!

Top guest favourite

Guesthouse in Kihei

4.98 out of 5 average rating, 87 reviews

Stunning remodeled treehouse cottage with views

Our cozy cottage is close to the beach, family-friendly activities, nightlife, public transport, tennis court, gym, shopping, bike rentals, and much much more right in central Kihei. Hosts live on property and are extremely accommodating and helpful. Enjoy the partial view of the ocean and spectacular morning views of Haleakala. The private outdoor patio/lanai is ideal for private sunset views, and meals. Licensed with the County of Maui B&B License BBKM20090013 TMK (2) 3-9-033:019

4.88 out of 5 average rating, 52 reviews

Condo in Wailuku

Great Listing and Price!

Come on over and sit in a lounge chair on the water's edge, watch the turtles in the water right in front of you, read a book or snooze to the sound of the waves. Check the calendar and reserve now! "My place is close to the airport, art and culture, parks, and great views" say the owners, the LeMotts. "You’ll love my place because of the coziness, the views, the location, and the people. My place is good for couples, solo adventurers, business travelers, and families (with kids)."

4.91 out of 5 average rating, 110 reviews

Full Ocean- Full Sunsets- Beaches at Royal Mauiian

Hawaii License: T-174-283-2640 Full ocean & beach front - all year sunsets. Royal Mauiian - Highly sought location in S. Kihei. Nicely done 1 BR - 1 BTH Nicely furnished, very streamlined open feel. Recently replaced bed. Walk to restaurants, steps to Kam 1 beach, close to many shops & activities. Rent a paddleboard, buy Hawaiian memorabilia, or shop at Harvest Moons - just across the street. Split Air in Bedroom & Living Area. Fully equipped kitchen. In Unit Laundry

4.83 out of 5 average rating, 146 reviews

Condo in Wailea

Beautiful Palms At Wailea #608-May/June Discount

Beautiful Palms At Wailea ,2BR/2BA,Condo, located in the heart of Wailea. 5* location. Vinyl wood flooring & Split Air-Cond. system in hallway & in master-B/R. Fans through-out. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., wide open floor plan ,2nd. fl.unit. Low rise complex. Very private. Large lanai . Barbecue grills located near entryway of complex. Views from the Club House & Pool.The best place to stay!

4.91 out of 5 average rating, 209 reviews

Condo in Wailuku

Rare Beachfront Ground floor Oceanview from Lanai!

Enjoy a Romantic yet affordable Direct BeachFront, Ground floor condo with a partial ocean view from the Lanai. NOT ACROSS THE STREET FROM THE OCEAN! Located on gorgeous Sugar Beach, Maalaea- the LONGEST WALKING BEACH on the entire island. Humpback Whales (Nov-April) and turtles are often seen in the waters. On a a quiet, non-through road, this is like your own little neighborhood paradise! GE-210-827-7760-01 TA-210-827-7760-01 General Excise/Transient Tax

5 out of 5 average rating, 7 reviews

Apartment in Kihei

Oceanview updated condo w/AC @ beachfront resort

Welcome to Nani Kai Hale 305. Enjoy an ocean view from your private lanai. Feel right at home in this updated condo with everything from split AC in both the living room and bedroom, sofa sleeper, fully equipped kitchen, beach gear, & essentials. This condo can comfortably accommodate 4 guests with its 2 full bathrooms. Situated on a 6 mile stretch of sandy beach in N Kihei the possibilities are endless for ocean activities. Book today!

4.87 out of 5 average rating, 187 reviews

Relaxing Kihei Condo right on the Beach in Maui

Escape to a ocean view condo right on a white sandy beach! Sunsets with inviting central AC, pool, spa, WiFi and fully equipped kitchen where you'll be sure to feel right at home. Enjoy breakfast on the balcony or tuck in and watch your favorite shows on the 2 flat screen smart TVs. Delicious local restaurants. Play tennis, mini golf, hit the sauna or grill some Ahi on the outdoor BBQs. Private free parking, beach equipment and sauna.